DE2220249A1 - 3-Halogenindazole und ihre Verwendung als Herbizide, Fungizide und Bakterizide - Google Patents

3-Halogenindazole und ihre Verwendung als Herbizide, Fungizide und Bakterizide

Info

Publication number: DE2220249A1
Authority: DE; Germany
Prior art keywords: chloroindazole; percent; mol; haloindazoles; methyl
Prior art date: 1971-05-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

DE19722220249

Other languages

German (de)

English (en)

Inventor

Pasquale Paul Woodside N.Y. Minieri (V.StA.)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tenneco Chemicals Inc

Original Assignee

Tenneco Chemicals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1971-05-10

Filing date

1972-04-25

Publication date

1972-11-23

1972-04-25 Application filed by Tenneco Chemicals Inc filed Critical Tenneco Chemicals Inc

1972-11-23 Publication of DE2220249A1 publication Critical patent/DE2220249A1/de

Status Pending legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title claims description 8
239000000417 fungicide Substances 0.000 title claims description 7
239000003899 bactericide agent Substances 0.000 title claims description 5
230000000844 anti-bacterial effect Effects 0.000 title claims description 4
-1 3,4-dichlorobenzoyl Chemical group 0.000 claims description 20
VWJQUUURHTZMKZ-UHFFFAOYSA-N 2-chloro-1-(3-chloroindazol-1-yl)ethanone Chemical compound ClCC(=O)N1N=C(C2=CC=CC=C12)Cl VWJQUUURHTZMKZ-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
230000002363 herbicidal effect Effects 0.000 claims description 3
230000000855 fungicidal effect Effects 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
239000003973 paint Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 12
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000001035 drying Methods 0.000 description 9
QPHAGNNWDZSKJH-UHFFFAOYSA-N 3-chloro-2h-indazole Chemical compound C1=CC=CC2=C(Cl)NN=C21 QPHAGNNWDZSKJH-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
YWBXPVJEXHNXLT-UHFFFAOYSA-N (3-chloroindazol-1-yl)methanol Chemical compound OCN1N=C(C2=CC=CC=C12)Cl YWBXPVJEXHNXLT-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
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WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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229910052799 carbon Inorganic materials 0.000 description 3
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230000000694 effects Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
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229910052757 nitrogen Inorganic materials 0.000 description 3
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RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
235000001674 Agaricus brunnescens Nutrition 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
HYYIHTQUNPPZIX-UHFFFAOYSA-N 2-(3-chloroindazol-1-yl)ethanol Chemical compound OCCN1N=C(C2=CC=CC=C12)Cl HYYIHTQUNPPZIX-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
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229920001817 Agar Polymers 0.000 description 1
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244000075850 Avena orientalis Species 0.000 description 1
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244000063299 Bacillus subtilis Species 0.000 description 1
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241000217446 Calystegia sepium Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
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244000068988 Glycine max Species 0.000 description 1
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206010061217 Infestation Diseases 0.000 description 1
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CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
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241001361634 Rhizoctonia Species 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
241000219793 Trifolium Species 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
229910000004 White lead Inorganic materials 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000012241 calcium silicate Nutrition 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000011534 incubation Methods 0.000 description 1
150000002473 indoazoles Chemical class 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 1
GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000001699 lower leg Anatomy 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000009526 moderate injury Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
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229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
239000002383 tung oil Substances 0.000 description 1
239000002966 varnish Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

DE19722220249 1971-05-10 1972-04-25 3-Halogenindazole und ihre Verwendung als Herbizide, Fungizide und Bakterizide Pending DE2220249A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US14199971A	1971-05-10	1971-05-10

Publications (1)

Publication Number	Publication Date
DE2220249A1 true DE2220249A1 (de)	1972-11-23

Family

ID=22498153

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19722220249 Pending DE2220249A1 (de)	1971-05-10	1972-04-25	3-Halogenindazole und ihre Verwendung als Herbizide, Fungizide und Bakterizide

Country Status (13)

Country	Link
US (1)	US3741979A (it)
AT (1)	AT315988B (it)
BE (1)	BE782528A (it)
BR (1)	BR7202555D0 (it)
CA (1)	CA978972A (it)
CH (1)	CH546537A (it)
DE (1)	DE2220249A1 (it)
ES (1)	ES401846A1 (it)
FR (1)	FR2139265A5 (it)
GB (1)	GB1383369A (it)
IT (1)	IT954419B (it)
NL (1)	NL7205064A (it)
ZA (1)	ZA721741B (it)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3637736A (en) *	1966-10-25	1972-01-25	Tenneco Chem	N'-substituted-6-nitroindazoles

1971
- 1971-05-10 US US00141999A patent/US3741979A/en not_active Expired - Lifetime
1972
- 1972-03-14 ZA ZA721741A patent/ZA721741B/xx unknown
- 1972-03-17 GB GB1275772A patent/GB1383369A/en not_active Expired
- 1972-04-11 IT IT49522/72A patent/IT954419B/it active
- 1972-04-14 NL NL7205064A patent/NL7205064A/xx unknown
- 1972-04-18 ES ES401846A patent/ES401846A1/es not_active Expired
- 1972-04-21 BE BE782528A patent/BE782528A/xx unknown
- 1972-04-21 CA CA140,303A patent/CA978972A/en not_active Expired
- 1972-04-25 DE DE19722220249 patent/DE2220249A1/de active Pending
- 1972-04-25 CH CH612472A patent/CH546537A/fr not_active IP Right Cessation
- 1972-04-26 BR BR2555/72A patent/BR7202555D0/pt unknown
- 1972-04-27 AT AT371572A patent/AT315988B/de active
- 1972-04-27 FR FR7215133A patent/FR2139265A5/fr not_active Expired

Also Published As

Publication number	Publication date
NL7205064A (it)	1972-11-14
BR7202555D0 (pt)	1973-05-03
ZA721741B (en)	1973-03-28
US3741979A (en)	1973-06-26
FR2139265A5 (it)	1973-01-05
CH546537A (fr)	1974-03-15
IT954419B (it)	1973-08-30
BE782528A (fr)	1972-08-16
ES401846A1 (es)	1975-03-01
GB1383369A (en)	1974-02-12
AT315988B (de)	1974-06-25
CA978972A (en)	1975-12-02

Publication	Publication Date	Title
DE2212268C3 (de)	1979-09-13	N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen
EP0199047B1 (de)	1988-10-05	Neue Iodpropargylether, ein Verfahren zu ihrer Herstellung und ihre Verwendung
DE2422763A1 (de)	1974-12-05	Biozide zusammensetzungen
DE2227012C2 (de)	1982-12-23	3-(2,4-Dichlor-5-propargyloxyphenyl)-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und die Zusammensetzungen, die es enthält
DE3019497A1 (de)	1981-11-26	Aminopropiophenon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE1620004A1 (de)	1970-02-12	Verfahren zur Herstellung von Aminoitroalkanen
CH380734A (de)	1964-08-15	Verfahren zur Herstellung von neuen s-Triazinderivaten
DE1908097A1 (de)	1969-09-11	Schaedlingsbekaempfungsmittel
DE1900125B2 (de)	1979-04-05	Substituierte Pyrazolone, Verfahren zu ihrer Herstellung und fungizide Zusammensetzungen
DE2145418A1 (de)	1973-03-15	Arylazo-thiocarbonsaeure-dialkylamide
DE2527639A1 (de)	1976-01-15	2,3-dihydro-1,4-dithiin-1,1,4,4tetroxid-antimikrobielle mittel
DE2426653C3 (de)	1982-05-06	Derivate des 2-Amino-1,3-thiazins
DE2136923A1 (de)	1973-02-01	Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide
CH637386A5 (de)	1983-07-29	Benzoxazol- und benzothiazolderivate.
EP0040740A2 (de)	1981-12-02	Aminopropanol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
DE2220249A1 (de)	1972-11-23	3-Halogenindazole und ihre Verwendung als Herbizide, Fungizide und Bakterizide
DE2221500C3 (de)	1975-06-05	3-Pyridylisothioharnstoffderivate, Verfahren zu deren Herstellung und ihre Verwendung als Mikrobizide
DE2419017A1 (de)	1974-11-07	Isothiazolin-3-one
DE1567211A1 (de)	1970-07-16	Fungicide und bactericide Mittel
DE2511311A1 (de)	1975-09-18	N-substituierte aminoacetamide, verfahren zu deren herstellung und fungizide mittel
DE1300117B (de)	1969-07-31	5-Sulfonyl-1, 2-dithiol-3-one
DE2220248A1 (de)	1973-05-30	Indazolylderivate und ihre verwendung als fungizide und bakterizide
DE2008622A1 (de)	1970-09-03	Phthalsäurezinnester, ihre Verwendung als Biozide in bioziden Mitteln und Anstrichmitteln
DE1951274A1 (de)	1970-04-16	Organozinnverbindungen und ihre Verwendung als Biocide
DE1204878B (de)	1965-11-11	Akarizide Mittel